Trichloroacetyl chloride → HCID 60026691, compound

HRID 400675Notes

Reaction equation

HRID 400675 reaction equation
[Cl:1]C(Cl)(Cl)C(Cl)=O.[F:8][C:9]([F:36])([F:35])[C:10]([CH2:25][C:26]1[NH:34][C:33]2[CH:32]=[CH:31][N:30]=[CH:29][C:28]=2[CH:27]=1)([OH:24])[CH2:11][C:12]([C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[O:22][CH3:23])([CH3:14])[CH3:13]>CN(C=O)C>[Cl:1][C:27]1[C:28]2[CH:29]=[N:30][CH:31]=[CH:32][C:33]=2[NH:34][C:26]=1[CH2:25][C:10]([OH:24])([CH2:11][C:12]([C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[O:22][CH3:23])([CH3:14])[CH3:13])[C:9]([F:35])([F:8])[F:36]

Participants

4

Reactant 2

HCID 6420Trichloroacetyl chlorideHCID 11495227HCID 11495227, compound

Product 1

HCID 60026691HCID 60026691, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of trichloroacetyl chloride (0.045 mL, 0.403 mmol) in 0.5 mL of DMF was treated with a solution of 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)pentan-2-ol (33.0 mg, 0.081 mmol) in 0.5 mL of DMF at room temperature. After 2 days, the reaction was quenched with 2 mL of ice-water and 2 mL of cold 1 N sodium hydroxide solution. The resulting mixture was extracted with three 5 mL portions of ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. Chromatography on SiO2 (100% dichloromethane to 10% methanol in dichloromethane, gradient) gave 20.0 mg of the title product (56% yield).

Workup

  1. customthe reaction was quenched with 2 mL of ice-water and 2 mL of cold 1 N sodium hydroxide solution
  2. extractionThe resulting mixture was extracted with three 5 mL portions of ethyl acetate
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f27bcbed56447e499080754023fd183
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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